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Total synthesis and structure revision of chrysamide B

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Abstract

Total synthesis of the originally proposed chrysamide B (2) is described, which features a convergent assembly of the chiral piperazine core and epoxy-acid. Mismatched spectroscopic data for the synthetic sample compared to that for the isolate led us to propose the revised structure 3 based on biosynthetic considerations. In a further antibacterial assay, chrysamide B and its diastereomer 2 exhibited different activities.

Graphical abstract: Total synthesis and structure revision of chrysamide B

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Publication details

The article was received on 01 Sep 2018, accepted on 06 Oct 2018 and first published on 08 Oct 2018


Article type: Research Article
DOI: 10.1039/C8QO00949J
Citation: Org. Chem. Front., 2018, Advance Article
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    Total synthesis and structure revision of chrysamide B

    J. Chen, J. Li, L. Zhu, X. Peng, Y. Feng, Y. Lu, X. Hu, J. Liang, Q. Zhao and Z. Wang, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00949J

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